CAS: 66701-25-5; (2S,3S)-3-(((S)-1-((4-Guanidinobutyl)Amino)-4-Methyl-1-Oxopentan-2-yl)Carbamoyl)Oxirane-2-Carboxylic Acid

该化合物是一种合成化合物,具有类似于状结构的典型特征;该物质具有过氧化物功能组,有助于其反应,特别是在生物系统中,因为它可能与核糖核素发生相互作用;一个guanidino组的存在表明潜在的生物活动,因为guanidino化合物经常参与酶抑制或调节;L-L-Leuucylamido成分表明,它来自氨基酸蕾西内,可能影响其与生物受体或酶的相互作用;此外,总体结构表明,该物质可能拥有与药用化学有关的特性,特别是在针对特定生物路径的治疗剂的开发方面;其稳定性,溶性和再活性取决于周围的条件,例如pH和温度,使它成为对药物学和生物化学学进一步研究的兴趣组合.

结构式图片

欧盟法规

C&L通报REACH预注册

合成工艺路线路线简述

    海关参考信息

    专利信息


    专利号:US-2006154325-A1
    优先权日:2005-01-10
    标题 :Synthesis of epoxide based inhibitors of cysteine proteases
    发明人:BOGYO MATTHEW; VERHELST STEVEN H
    权利人:BOGYO MATTHEW; VERHELST STEVEN H
    摘要:Epoxide based cysteine protease inhibitors containing peptide derivatives and methods for synthesizing them in sold phase are disclosed. Preferably, an epoxy succinyl “warheadâ€? (for binding to the enzyme) is prepared, having two amino acid residues or residue-like structures on either side. Natural and non-natural amino acids may be used. The present process may be carried out entirely on a solid support, with the proviso that a dipeptide like group is prepared prior to coupling to one side of the supported complex. The method lends itself to more efficient inhibitor synthesis, and may be employed with mixtures of peptide compounds, and various modifications of epoxides to create diverse libraries of inhibitors.
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    主要参考文献


    1: Blass G, Levchenko V, Ilatovskaya DV, Staruschenko A. Chronic cathepsin inhibition by E-64 in Dahl salt-sensitive rats. Physiol Rep. 2016 Sep;4(17). pii: e12950. doi: 10.14814/phy2.12950.
    2: Wilder CL, Walton C, Watson V, Stewart FA, Johnson J, Peyton SR, Payne CK, Odero-Marah V, Platt MO. Differential cathepsin responses to inhibitor-induced feedback: E-64 and cystatin C elevate active cathepsin S and suppress active cathepsin L in breast cancer cells. Int J Biochem Cell Biol. 2016 Oct;79:199-208. doi: 10.1016/j.biocel.2016.08.030. Epub 2016 Aug 31.
    3: Kershaw CM, Evans G, Rodney R, Maxwell WM. Papain and its inhibitor E-64 reduce camelid semen viscosity without impairing sperm function and improve post-thaw motility rates. Reprod Fertil Dev. 2016 May 9. doi: 10.1071/RD15261. [Epub ahead of print] doi: 10.1155/2015/134242. Epub 2015 Jul 9.

    合成参考文献


    参考文献:10.1021/jm900946n
    摘要:Breuning A, Degel B, Schulz F, Büchold C, Stempka M, Machon U, Heppner S, Gelhaus C, Leippe M, Leyh M, Kisker C, Rath J, Stich A, Gut J, Rosenthal PJ, Schmuck C, Schirmeister T. Michael acceptor based antiplasmodial and antitrypanosomal cysteine protease inhibitors with unusual amino acids. J Med Chem. 2010 Mar 11;53(5):1951–63. doi: 10.1021/jm900946n.
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